Licensing and Distributing a Paid CLI With Ruby, Rails, and SwiftUI
summary
A paid CLI called Ruby on Mac enforces one year of updates and a one‑Mac limit by shipping a signed license file and self‑contained binaries built with ruby‑packer and shc and delivered as a .pkg; Paddle webhooks, a Rails backend and ActiveStorage generate GitLab‑style signed licenses, and Apple’s DeviceCheck API verifies device activations. The rollout mostly works after rewriting bash into Ruby to avoid antivirus false positives (SentinelOne) and handling Macs without Secure Enclave; 15 discount codes exist.
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chapters (17)
- 0:00Ruby installation struggles
- 4:56Ruby on Mac features
- 7:43Licensing system requirements
- 10:11Compile Ruby to binaries
- 14:28OpenSSL troubleshooting
- 18:01Certificate locations on Macs
- 20:05DeviceCheck and restrictions
- 22:59MacOS app for token generation
- 25:03Code signing and verification
- 27:52Perpetual fallback licenses
- 29:18Webhook timing in Rails
- 31:49License verification flow
- 33:15HTTP timeout optimization
- 34:42Demo: license verification
- 36:50Antivirus issues with Bash
- 38:14Bash to Ruby rewrite
- 40:00Q&A
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